Tag: M.W:100-200

Electric Literature of 1033810-70-6 , The common heterocyclic compound, 1033810-70-6, name is [1,2,4]Triazolo[1,5-a]pyridin-7-ol, molecular formula is C6H5N3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Step F: Preparation of tert-butyl 4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-chloro-2-fluorobenzoate: A vial charged with tert-butyl 3-chloro-2,4-difluorobenzoate (0.210 g, 0.845 mmol), [1,2,4]triazolo[1,5-a]pyridin-7-ol (0.114 g, 0.845 mmol), cesium carbonate (0.413 g, 1.27 mmol), and DMF (1.7 ml). The reaction was heated to 80 C for 12 hours, then poured into ice water. The resulting solids were collected by filtration and purified by flash chromatography, eluting with gradient of 10% EtOAc/ Hexanes to 50% EtOAc/Hexanes to provide the desired product.

The synthetic route of 1033810-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Array Biopharma, Inc.; EP2090575; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Ethyl 6-Chloropyridine-3-acetate

Step 2 To a solution of ethyl 2-(6-chloropyridin-3-yl)acetate (1.1 g, 5.51 mmol) in dimethylformamide was added slowly sodium hydride (242 mg, 6.06 mmol) at 0 C., followed by iodomethane (821 mg, 5.79 mmol). The mixture was stirred at same degree for 1 hour, and then quenched with water. The resulting mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(6-chloropyridin-3-yl)propanoate (790 mg, 67%).

With the rapid development of chemical substances, we look forward to future research findings about 197376-47-9.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29962; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1186608-73-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1186608-73-0, name is 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine, molecular formula is C7H8N4, molecular weight is 148.17, as common compound, the synthetic route is as follows.

EXAMPLE 16: Tetra-butyl 3-(3-methyl-lH-pyrazolo r3.4-blpyridine-5- ylamino)piperidine- 1 -carboxylateTo a stirred solution of 3-Methyl-lH-pyrazole[3,4-¾]pyridn-5-amine (500mg, 3.3mmol) in EtOH (50ml), tert-butyl 3 -oxopiperidine-1 -carboxylate (74mg, l . lmmol) was added and reaction mass was cooled to 0C. Acetic acid (0.018ml, 0.33mmol) was added after which reaction mixture was stirred for 20 minutes. Sodium cyanoborohydride (42mg, 0.66mmol) was added and stirred for 12h at RT. TLC showed absence of SM. The reaction mixture was quenched with brine solution and extracted with ethyl acetate. The extract was washed with water and concentrated. Organic layer was dried over anhydrous sodium sulphate, dried and concentrated. Product was purified by flash column chromatography over 230-400 mesh silica gel using 2-5% MeOH/ DCM as eluent to afford the desired product 20, 500mg (Yield: 45%) as white solid. The product was confirmed by 1HNMR and MS spectrum analysis. 1H NMR (400 MHz, CDC13) delta: 8.13 (s, 1H), 7.19 (s, 1H), 3.95 (m, 1H), 3.25 (m, 1H), 3.43 (m, 1H), 3-3.25 (m, 2H), 2.52 (s, 3H), 2.15 (m. 1H), 1.78 (m, 1H), 1.6 (m, 2H), 1.49 (s, 9H); Ms- 331 (M-56), LCMS- 97%.

Statistics shows that 1186608-73-0 is playing an increasingly important role. we look forward to future research findings about 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine.

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 76015-11-7 ,Some common heterocyclic compound, 76015-11-7, molecular formula is C7H9NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

a 2-Methyl-3-methoxy-4-chloropyridine N-oxide 11.2 g (80.5 mmol) of 3-methoxy-2-methyl-4(1H)-pyridone were heated under reflux for 10 hours in 100 ml of phosphorus oxychloride. Subsequently, the mixture was concentrated and 30 ml of toluene were added to each 2 ml volume; concentration then took place once again and the residue was taken up in 150 ml of water, with the pH of the mixture then being adjusted to 11 with K2 CO3; this mixture was then extracted with dichloromethane and the organic phase was washed with water, dried and freed from solvent. 8 g of the product were obtained, under standard conditions, from the pale brown oil (9 g) using m-chloroperbenzoic acid in dichloromethane, m.p. 88-89 C. (from petroleum ether).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76015-11-7, its application will become more common.

Reference:
Patent; Hoechst Aktiengesellschaft; US5658933; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 62226-18-0, Adding some certain compound to certain chemical reactions, such as: 62226-18-0, name is 6-Chlorothieno[2,3-b]pyridine,molecular formula is C7H4ClNS, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 62226-18-0.

EXAMPLE 70 6-Chloro-thieno[2,3-b]pyridine-2-sulfonyl chloride 6-Chloro-thieno[2,3-b]pyridine (0.73 g, 4.3 mmol) is to subjected to the three step sequence sequence described in EXAMPLE 8, Part A. Flash chromatography (15 % EtOAc/Hexane) of the crude product gives the title compound (0.75 g, 2.8 mmol): 1H NMR (CDCl3, 300 MHz) delta8.19 (d, 1H), 8.07 (s, 1H), 7.47 (d, 1H). EI MS M+=267, 269, 271.

According to the analysis of related databases, 62226-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma Deutschland GmbH; US6281227; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. A new synthetic method of this compound is introduced below., name: Ethyl 6-Chloropyridine-3-acetate

To a solution of ethyl (6-chloropyridin-3-yl)acetate (1.0 g) in N,N-dimethylformamide (20 mL) was added sodium hydride (60% in mineral oil, 0.40 g) under ice-cooling, and the mixture was stirred for 40 min. To the reaction mixture was added 1-bromo-2-(2-bromoethoxy)ethane (2.3 g), and the mixture was stirred at 0 C. for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.82 g). (1596) MS(ESI+): [M+H]+ 270.1

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 197376-47-9, Ethyl 6-Chloropyridine-3-acetate.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, molecular weight is 143.57, as common compound, the synthetic route is as follows.category: pyridine-derivatives

(Step 6) Preparation of 8-(6-tert-butyl-1H-benzo[d]imidazol-2-yl)-4-(5-methoxypyridin-2-yl)-3,4-dihydro-2H-benzo[b][1,4-]oxazine To a solution of 4-(5-tert-butyl-1H-benzo[d]imidazol-2-yl)benzene amine 3.1 g (10 mmol) in toluene 10 mL were added 2-chloro-5-methoxy pyridine 1.5 g (10 mmol), Pd(OAc)2 0.1 g (0.5 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 0.5 g (0.8 mmol) and Cs2CO3 4.6 g (14 mmol), followed by stirring at 90 C. for 12 hrs. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and diluted with ethylacetate. The product thus formed was washed with a saturated sodium bicarbonate solution and a saturated NaCl solution, dried over magnesium sulfate and concentrated in a vacuum. The residue was purified by column chromatography (developing solvent: ethylacetate/hexane=2/3) to give 3.5 g of the title compound (yield 85%). 1H NMR (MeOD-d4) delta: 8.04 (d, 1H, J=3.0 Hz), 7.79 (dd, 2H, J=7.8, 1.5 Hz), 7.67 (d, 1H, J=1.7 Hz), 7.56 (d, 1H, J=8.6 Hz), 7.38 (m, 2H), 7.25 (d, 1H, J=9.0 Hz), 7.17 (dd, 1H, J=8.1, 1.4 Hz), 6.95 (t, 1H, J=8.0 Hz), 4.52 (t, 2H, J=4.4 Hz), 3.99 (t, 2H, J=4.4 Hz), 3.86 (s, 3H), 1.41 (s, 9H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139585-48-1, 2-Chloro-5-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Daewoong Pharmaceutical Co., Ltd.; US8026235; (2011); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 81803-60-3, Ethyl imidazo[1,5-a]pyridine-3-carboxylate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 81803-60-3, blongs to pyridine-derivatives compound. Recommanded Product: 81803-60-3

2-(Aminomethyl)pyridine (1.5 g, 13.9 mmol) and pyridine (5.55 g, 59.6 mmol) were dissolved in MeCN (30 mL), and the solution was cooled by using an ice bath. A solution of ethyl oxalyl chloride (1.89 g, 13.9 mmol) in MeCN (10 mL) was added dropwise at 0 to -5 C. After the addition, the mixture was stirred for 2 h and a solution of TFAA (6.41 g, 30.5 mmol) in MeCN (15 mL) was added dropwise at -15 to -10 C (ice-salt bath). The reaction mixture was allowed to stand overnight in the bath, then the mixture was poured in sat. aq sodium hydrocarbonate, filtered, and washed with water. Yield: 3.77 g (95%); yellow solid; mp 225 C. 1H NMR (DMSO-d6): delta = 1.40 (t, J = 6.6 Hz, 3 ), 4.48 (q, J = 6.6 Hz, 2 H), 7.51 (t, J = 6.6 Hz, 1 H), 7.86 (t, J = 7.6 Hz, 1 H), 8.40 (d, J = 8.8 Hz,1 H), 9.45 (d, J = 6.6 Hz, 1 H). 13C NMR (DMSO-d6): delta = 14.2, 61.7, 116.6 (q, 1JC-F = 290.7 Hz), 118.5, 118.6, 123.1, 128.0, 129.1, 132.2, 139.0, 158.4, 172.9 (q, 2JC-F = 33.9 Hz). MS: m/z (%) = 288 (14) [M + 2]+, 287 (100) [M + 1]+, 259 (3) [M + 2 -CO]+, 242 (3) [M + 2 – C2H5OH]+, 241 (23) [M + 1 – C2H5OH]+.

The synthetic route of 81803-60-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tverdiy, Dmytro O.; Chekanov, Maksym O.; Savitskiy, Pavlo V.; Syniugin, Anatolii R.; Yarmoliuk, Sergiy M.; Fokin, Andrey A.; Synthesis; vol. 48; 23; (2016); p. 4269 – 4277;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13210-52-1, 1-(3-Aminopyridin-4-yl)ethanone, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Safety of 1-(3-Aminopyridin-4-yl)ethanone, blongs to pyridine-derivatives compound. Safety of 1-(3-Aminopyridin-4-yl)ethanone

To a solution of 1-(3-aminopyridin-4-yl)ethanone (0.9 g, 6.61 mmol) in DMF (10 mL) was added NBS (2.53 g, 14.21 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate and saturated NaHCO3 solution. The organic layers (extracted two times) were washed with saturated NaHCO3 solution, dried over MgSO4. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography. The product was eluted with 0-20% ethyl acetate in hexane to give the desired product as a white solid (1.55 g, 80%); HPLC: RT=0.88 min (H2O/ACN with 0.05% TFA, Waters Acquity SDS C18, 2.1×50 mm, 1.7-mum particles, gradient=1.8 min, wavelength=220 nm); MS (ES): m/z=292.8, 294.8 [M+H]+; 1H NMR (400 MHz, CDCl3) delta ppm 7.65 (s, 1H), 6.73 (br. s., 2H), 2.62 (s, 3H).

The synthetic route of 13210-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; Fink, Brian E.; Zhao, Yufen; Borzilleri, Robert M.; Zhang, Liping; Kim, Kyoung S.; Kamau, Muthoni G.; Tebben, Andrew J.; (162 pag.)US2016/176871; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 562825-95-0, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 562825-95-0, name is N-Ethyl-3-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Preparation of N4-ethylpyridine-3,4-diamineHN.>. “2Ethyl-(3-nitropyridin-4-yl)amine (8.7g, 52.0mmol) in ethanol (150ml) was hydrogenated for 18 hours in the presence of 10% palladium on carbon. After filtration of the catalyst through celite, the filtrate was concentrated in vacuo to afford the title compound (6.7g, 94%). 1H NMR (400 MHz, DMSO-D6) delta ppm 1.19 (m, 3H), 3.09 (m, 2H), 4.53 (br, 2H),5.21 (br, 1 H), 6.31 (d, J=5.22 Hz, 1 H), 7.57 (d, J=5.36 Hz, 1 H), 7.62 (s, 1 H). MS (ES+) m/e 138 [M+H]+.

According to the analysis of related databases, 562825-95-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/63167; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem